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Chicago

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Chicago Flights as Low as $56

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, May 7 - Tue, May 14
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$56 Roundtrip, found 6 days ago
$56
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, May 7 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 14, priced at $56 found 6 days ago
Frontier Airlines
Tue, May 14 - Mon, May 20
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$57 Roundtrip, found 3 days ago
$57
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, May 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, May 20, priced at $57 found 3 days ago
Frontier Airlines
Tue, Apr 30 - Sat, May 4
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$58 Roundtrip, found 3 days ago
$58
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Apr 30 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, May 4, priced at $58 found 3 days ago
Frontier Airlines
Wed, May 15 - Tue, May 21
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$60 Roundtrip, just found
$60
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, May 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 21, priced at $60 just found
Spirit Airlines
Tue, May 7 - Wed, May 8
LGA
LaGuardia
ORD
O'Hare Intl.
$61 Roundtrip, just found
$61
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, May 7 from LaGuardia to O'Hare Intl., returning Wed, May 8, priced at $61 just found
Spirit Airlines
Wed, May 15 - Tue, May 21
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, just found
$63
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, May 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 21, priced at $63 just found
Spirit Airlines
Sun, May 12 - Wed, May 15
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 3 days ago
$63
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sun, May 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, May 15, priced at $63 found 3 days ago
Frontier Airlines
Tue, May 7 - Tue, May 14
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, May 7 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, May 14, priced at $68 just found
Frontier Airlines
Tue, Apr 30 - Wed, May 8
LGA
LaGuardia
MDW
Midway Intl.
$106 Roundtrip, found 1 day ago
$106
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Apr 30 from LaGuardia to Midway Intl., returning Wed, May 8, priced at $106 found 1 day ago
United
Tue, May 28 - Wed, May 29
LGA
LaGuardia
ORD
O'Hare Intl.
$117 Roundtrip, just found
$117
Roundtrip
just found
Select United flight, departing Tue, May 28 from LaGuardia to O'Hare Intl., returning Wed, May 29, priced at $117 just found
Delta
Tue, May 28 - Wed, May 29
LGA
LaGuardia
ORD
O'Hare Intl.
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Delta flight, departing Tue, May 28 from LaGuardia to O'Hare Intl., returning Wed, May 29, priced at $117 just found
American Airlines
Wed, May 15 - Tue, May 21
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$139 Roundtrip, just found
$139
Roundtrip
just found
Select American Airlines flight, departing Wed, May 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 21, priced at $139 just found
Delta
Tue, May 7 - Tue, May 14
DAL
Love Field
MDW
Midway Intl.
$198 Roundtrip, just found
$198
Roundtrip
just found
Select Delta flight, departing Tue, May 7 from Love Field to Midway Intl., returning Tue, May 14, priced at $198 just found
Delta
Tue, May 7 - Tue, May 14
DAL
Love Field
ORD
O'Hare Intl.
$198 Roundtrip, just found
$198
Roundtrip
just found
Select Delta flight, departing Tue, May 7 from Love Field to O'Hare Intl., returning Tue, May 14, priced at $198 just found
JetBlue Airways
Tue, May 28 - Wed, May 29
LGA
LaGuardia
ORD
O'Hare Intl.
$269 Roundtrip, just found
$269
Roundtrip
just found
Select JetBlue Airways flight, departing Tue, May 28 from LaGuardia to O'Hare Intl., returning Wed, May 29, priced at $269 just found
Sun Country Airlines
Fri, May 24 - Mon, May 27
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$313 Roundtrip, found 5 days ago
$313
Roundtrip
found 5 days ago
Select Sun Country Airlines flight, departing Fri, May 24 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, May 27, priced at $313 found 5 days ago

Cheap Flights to Chicago

Fall in love at first flight with your vacation to Chicago by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chicago on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chicago, the good times start rolling. So buckle up, you’re in for a fun ride.

Just the right flight

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chicago with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

Frequently Asked Questions About flights to Chicago

What is the cheapest month to fly to Chicago?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chicago are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chicago?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Chicago.

What airport is best to fly into Chicago?

When you’re planning your trip to Chicago, convenience is the name of the game. Luckily, Chicago Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Chicago must-do list.

How much are flights to Chicago?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chicago on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $56, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chicago?

The trick to saving a stack of cash on your flight to Chicago? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $56 right now, why wait?

Can I fly to Chicago right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to  right now?” When it’s time to book your flight, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

Chicago Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$55

Last Minute Hotel Deals in Chicago

Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
The price is $91 per night from Apr 21 to Apr 22
$91
per night
Apr 21 - Apr 22
Stay at this 4-star boutique hotel in Chicago. Enjoy a 24-hour health club, onsite parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
7.8/10 Good! (1,008 reviews)
Bedbugs!!!! Terrible.
"Bedbugs were killing me and made me wake up middle of the night everyday. I need moneyback."

Reviewed on Apr 18, 2024

Hotel Felix River North/Magnificent Mile
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $143 per night from Apr 21 to Apr 22
$143
per night
Apr 21 - Apr 22
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (6,557 reviews)
"Clean and loved the classic grandiose decor. Unfortunately our room was connected to the other rooms on either side of us, and there was a large gap between the doors and the floor, meaning we could see light and hear all the noise (TV, even hear when the person was showering) from their room while ..."

Reviewed on Apr 19, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $129 per night from Apr 21 to Apr 22
$129
per night
Apr 21 - Apr 22
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,777 reviews)
"The front staff is amazing, had a last minute change of mind about the room I book and they upgraded us on spot. Everyone there is amazing and very helpful! The hotel its self is at a prime location and only a few minutes walk away from the attractions in Chicago. The valet service was good and very ..."

Reviewed on Apr 17, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
The price is $160 per night from Apr 21 to Apr 22
$160
per night
Apr 21 - Apr 22
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,851 reviews)
"Property was very nice"

Reviewed on Apr 18, 2024

Eurostars Magnificent Mile
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3 out of 5
243 E. Ontario, Chicago, IL
The price is $104 per night from Apr 28 to Apr 29
$104
per night
Apr 28 - Apr 29
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, breakfast, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (2,169 reviews)
"Convenience"

Reviewed on Apr 19, 2024

Aloft Chicago Mag Mile
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
The price is $119 per night from Apr 21 to Apr 22
$119
per night
Apr 21 - Apr 22
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and room service. Our guests praise the restaurant and the helpful staff ...
8.4/10 Very Good! (2,993 reviews)
Club quarters stay
"Wonderful staff! Close to trains and several restaurant options within walking distance."

Reviewed on Apr 16, 2024

Club Quarters Hotel, Central Loop, Chicago
InterContinental Chicago Magnificent Mile, an IHG Hotel
InterContinental Chicago Magnificent Mile, an IHG Hotel
4.5 out of 5
505 N Michigan Ave, Chicago, IL
The price is $199 per night from Apr 21 to Apr 22
$199
per night
Apr 21 - Apr 22
Stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
8.6/10 Excellent! (1,544 reviews)
"The location is great for visiting Downtown Chicago. It's right next to Tribune building, across from Wrigley building. Safe to walk around during the day. Car pickup and drop off is a bit challenging. Property is newly renovated, feels clean and modern in the historical building setting. We'll stay ..."

Reviewed on Apr 13, 2024

InterContinental Chicago Magnificent Mile, an IHG Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
The price is $146 per night from Apr 26 to Apr 27
$146
per night
Apr 26 - Apr 27
Stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,004 reviews)
"Excellent location. Easy walk to shops and sightseeing. Riverwalk is 15 min walk from hotel. Right next to former Hancock building."

Reviewed on Apr 17, 2024

The Westin Michigan Avenue Chicago
See all 4,944 properties in Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Hotels With Free Airport Shuttle

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
3 out of 5
777 East Grand Avenue, Bensenville, IL
The price is $75 per night from May 6 to May 7
$75
per night
May 6 - May 7
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.4/10 (1,001 reviews)
"We did a park and stay while we were on vacation!"

Reviewed on Apr 15, 2024

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Super 8 by Wyndham Chicago O'Hare Airport
Super 8 by Wyndham Chicago O'Hare Airport
2.5 out of 5
2951 Touhy Ave, Elk Grove Village, IL
The price is $76 per night from Apr 21 to Apr 22
$76
per night
Apr 21 - Apr 22
Stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (1,000 reviews)
"Refrigerator is always a must, they had that but no microwave. There was free breakfast, cereal and waffles. Matress had a dimple where everyone sleeps on that side."

Reviewed on Apr 15, 2024

Super 8 by Wyndham Chicago O'Hare Airport
Hampton Inn Chicago-O'Hare International Airport
Hampton Inn Chicago-O'Hare International Airport
2.5 out of 5
3939 N Mannheim Rd, Schiller Park, IL
The price is $114 per night from Apr 22 to Apr 23
$114
per night
Apr 22 - Apr 23
Stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,276 reviews)
"Good"

Reviewed on Apr 17, 2024

Hampton Inn Chicago-O'Hare International Airport
Holiday Inn Chicago O'Hare Area, an IHG Hotel
Holiday Inn Chicago O'Hare Area, an IHG Hotel
3 out of 5
5615 North Cumberland Avenue, Chicago, IL
The price is $103 per night from Apr 28 to Apr 29
$103
per night
Apr 28 - Apr 29
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast. Our guests praise the breakfast and the helpful staff in our reviews. ...
7.4/10 Good! (1,000 reviews)
"Clean hotel. Staff was friendly."

Reviewed on Apr 9, 2024

Holiday Inn Chicago O'Hare Area, an IHG Hotel
Loews Chicago O'Hare Hotel
Loews Chicago O'Hare Hotel
4.5 out of 5
5300 N River Rd, Rosemont, IL
The price is $199 per night from Apr 26 to Apr 27
$199
per night
Apr 26 - Apr 27
Stay at this 4.5-star luxury hotel in Rosemont. Enjoy free WiFi, breakfast, and a free airport shuttle. Our guests praise the restaurant and the helpful staff ...
9.2/10 Wonderful! (1,505 reviews)
"Great clean place Loved it!!"

Reviewed on Apr 14, 2024

Loews Chicago O'Hare Hotel
Carlton Inn Midway
Carlton Inn Midway
2 out of 5
4944 S Archer Ave, Chicago, IL
The price is $119 per night from Apr 20 to Apr 21
$119
per night
Apr 20 - Apr 21
Stay at this business-friendly motel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.2/10 Good! (1,000 reviews)
"The property was at a great location and close to shopping & events. Nice stay."

Reviewed on Apr 8, 2024

Carlton Inn Midway
See all 4,944 properties in Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.